191165-35-2Relevant academic research and scientific papers
A Novel and Practical Synthesis of L-Hexoses from D-Glycono-1,5-lactones
Takahashi, Hideyo,Hitomi, Yuko,Iwai, Yoshinori,Ikegami, Shiro
, p. 2995 - 3000 (2007/10/03)
A novel and efficient conversion of D-glycono-1,5-lactones into the corresponding L-sugars is described. The important intermediate, δ-hydroxyalkoxamates, was provided by a practical alkoxyamination of D-glycono-1,5-lactones mediated by Me3Al.
Cyclization dichotomy of D-xylo-hex-5-ulosonamides and synthesis of piperidine analogs of aldohexoses and aldohexono-1,5-lactones
Kovarikova, Radka,Ledvina, Miroslav,Saman, David
, p. 673 - 684 (2007/10/03)
The preparation of 2,3,4,6-tetra-O-benzyl-S-D-xylo-hex-5-ulosonamides 3a and 3b and their cyclization to 5-amino-2,3,4,6-tetra-O-benzyl-5-deoxy-D-glucono-1,5-lactam (4) and 5-amino-2,3,4,6-tetra-O-benzyl-S-deoxy-D-talono-1,5-lactam (5) or to 2,3,4,6-tetra
An efficient activation of the hydroxyl function by (diethylamino)sulfur trifluoride (DAST): preparation of chiral polyoxygenated tetrahydrofurans by stereoselective benzyloxy group participation
Monthiller, Sophie,Heck, Marie-Pierre,Mioskowski, Charles,Lafargue, Pierre,Lellouche, Jean-Paul,Masella, Michel
, p. 145 - 152 (2007/10/03)
Based on an intramolecular benzyloxy or amide group participation, two sets of experimental conditions have been established for the preparation of cis/trans tetrahydrofurans 6 or lactone 8 from sugar-derived open-chain hydroxylated precursors 4.These include: (1) a two-step mesylation-cyclization promoted by LiOH/THF-H2O or NaI/CH3CN at reflux; or (2) a one-step cyclization mediated by (diethylamino)sulfur trifluoride (DAST) at -78 deg C in CH2Cl2.The scope and limitations of these cyclizations are described particularly in relation to a stereoselective synthesis of highly oxygenated chiral tetrahydrofurans.Molecular modeling studies tentatively rationalized our experimental cyclization results affording five-membered versus six-membered heterocycles starting from different precursors. - Keywords: polyoxygenated tetrahydrofuran; (diethylamino)sulfur trifluoride (DAST); benzyl group participation; amide group participation; L-gulonolactone; differentially protected 1,4-diol
